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What Does Your Outfit Say About You?

My friend Kate came to town this weekend! We’d wanted to have a low-key, restful visit, but both Friday and Saturday nights, we stayed out until 5:30 a.m. None of it was planned...which means that twice I was caught wearing the wrong thing.

If there’s one place you can get snobby looks from women, it’s Dorrian’s, and I was a prime target in my office-appropriate attire (a button down RL shirt and J. Crew blazer—oy). The boys didn’t seem to notice that I was dressed more like them than the girls (although one guy did ask if I was a lesbian, based on my androgynous look and apparent fondness for Kate, whom I hadn't seen since Nantucket). Anyway, I met a hot guy in a rugby shirt. He had such an athletic body, you'd think he would only talk to a woman with the same, but I managed to prove you don’t have to show skin or hint at your physique (with tight clothing) in order to get attention.

Saturday, Kate and I stopped into a bar to check the USC football score. We had planned to go home afterwards to shower and get dolled up to go out, but we never did. I was wearing a tank top I usually sleep in, a hoodie sweatshirt, and no makeup. Kate was in a ball cap and corduroys. We sat next to a guy so good-looking I assumed he’d be a jerk. (I also assumed that the seat he was holding next to him was for his girlfriend. It turned out to be reserved for his male roommate, who had really pretty eyes and looked like Casey Affleck with a shaved head.) The four of us started chatting about the game and, through the course of the night, we did three rounds of shots and even went to another bar together. We all got along so well and exchanged numbers with each other at the end.

Bad bar outfit #2: It's a wonder they didn't card me in my hoodie, sans makeup (Is that why I look so washed out in the photo?). On the right, Kate in a cap.

In a bar, where first impressions are the only thing people have to go on, you could have easily overlooked me and/or assumed I was clueless, so it's funny that I could be successful, dressed for work (at 2 a.m.!) and dressed for bed.

And about assumptions: do you ever assume someone probably knows he's good-looking, or that someone has a girlfriend? And would you ever hit on a guy wearing the completely wrong thing (and you assumed he didn’t know better)?